Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles

doi:10.6023/cjoc201711014

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 846-854.DOI: 10.6023/cjoc201711014 Previous Articles Next Articles

Articles

低共熔溶剂催化一锅合成4,7-二氢-1H-吡唑并[3,4-b]吡啶-5-腈衍生物

高歌^a, 王萍^b, 刘鹏^a, 张卫红^a, 默丽萍^a, 张占辉^a

a 河北师范大学化学与材料科学学院化学国家级实验教学示范中心石家庄 050024;
b 河北化工医药职业技术学院化学与环境工程系石家庄 050026

收稿日期:2017-11-08 修回日期:2017-12-05 发布日期:2017-12-15
通讯作者: 张占辉 E-mail:zhanhui@hebtu.edu.cn,orgsynchem@sina.com.cn
基金资助:
国家自然科学基金（No.21272053）和河北省自然科学基金（No.B2015205182）资助项目.

Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles

Gao Ge^a, Wang Ping^b, Liu Peng^a, Zhang Weihong^a, Mo Liping^a, Zhang Zhanhui^a

a National Demonstration Center for Experimental Chemistry Education, College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024;
b Department of Chemical and Environmental Engineering, Hebei Chemical and Pharmaceutical Vocational Technology College, Shijiazhuang 050026

Received:2017-11-08 Revised:2017-12-05 Published:2017-12-15
Contact: 10.6023/cjoc201711014 E-mail:zhanhui@hebtu.edu.cn,orgsynchem@sina.com.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272053) and the Natural Science Foundation of Hebei Province (No. B2015205182).

1. Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles.PDF(840KB)

Abstract

Deep eutectic solvent based on L-proline and oxalic acid has been demonstrated for the first time as an efficient catalyst for synthesis of 4,7-dihydro-1H-pyrazolo[3,4-b] pyridine-5-carbonitrile derivatives via one-pot three-component reaction of aldehyde, 3-oxopropanenitrile and 1H-pyrazol-5-amine. The key features of this approach include the broad substrate scope, operational simplicity, recyclable catalyst and possibility to scale up giving multigram quantities.

Key words: deep eutectic solvent, multicomponent reaction, 4,7-dihydro-1H-pyrazolo[3,4-b] pyridine-5-carbonitrile, green chemistry

Cite this article

Gao Ge, Wang Ping, Liu Peng, Zhang Weihong, Mo Liping, Zhang Zhanhui. Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles[J]. Chin. J. Org. Chem., 2018, 38(4): 846-854.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Garbarino, S.; Ravelli, D.; Protti, S.; Basso, A. Angew. Chem., Int. Ed. 2016, 55, 15476.
[2] Xiong, X. Q.; Han, Q.; Shi, L.; Xiao, S. Y.; Bi, C. Chin. J. Org. Chem. 2016, 36, 480(in Chinese). (熊兴泉, 韩骞, 石霖, 肖上运, 毕成, 有机化学, 2016, 36, 480.)
[3] Zhang, Z. R.; Zheng, X. L.; Guo, C. B. Chin. J. Org. Chem. 2016, 36, 1241(in Chinese). (张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241.)
[4] Bai, R.; Yang, J.; Min, L.; Liu, C.; Wu, F.; Gu, Y. Tetrahedron 2016, 72, 2170.
[5] Taheri, A.; Lai, B.; Yang, J.; Zhang, J.; Gu, Y. Tetrahedron 2016, 72, 479.
[6] Chen, X.; Hu, C.; Wan, J.-P.; Liu, Y. Tetrahedron Lett. 2016, 57, 5116.
[7] Li, Y.; Zhao, B.; Du, B.; Jiang, Q.; Wang, X.; Cao, C. Tetrahedron Lett. 2013, 54, 227.
[8] Cao, S.; Jing, Y. F.; Liu, Y. Y.; Wan, J. P. Chin. J. Org. Chem. 2014, 34, 876(in Chinese). (曹硕, 景艳锋, 刘云云, 万结平, 有机化学, 2014, 34, 876.)
[9] Liu, Y. Y.; Wang, H.; Wan, J. P. Asian J. Org. Chem. 2013, 2, 374.
[10] Wan, J. P.; Liu, Y. Y. RSC Adv. 2012, 2, 9763.
[11] Zhang, Z. H.; Li, T. S. Curr. Org. Chem. 2009, 13, 1.
[12] Li, X. T.; Liu, Y. H.; Liu, X.; Zhang, Z. H. RSC Adv. 2015, 5, 25625.
[13] Leonardi, M.; Villacampa, M.; Menendez, J. C. J. Org. Chem. 2017, 82, 2570.
[14] Wu, J. S.; Zhang, X.; Zhang, Y. L.; Xie, J. W. Org. Biomol. Chem. 2015, 13, 4967.
[15] Dodiya, D. K.; Trivedi, A. R.; Kataria, V. B.; Shah, V. H. Curr. Org. Chem. 2012, 16, 400.
[16] Quiroga, J.; Villarreal, Y.; Galvez, J.; Ortiz, A.; Insuasty, B.; Abonia, R.; Raimondi, M.; Zacchino, S. Chem. Pharm. Bull. 2017, 65, 143.
[17] Lourenco, A. L.; Salvador, R. R. S.; Silva, L. A.; Saito, M. S.; Mello, J. F. R.; Cabral, L. M.; Rodrigues, C. R.; Vera, M. A. F.; Muri, E. M. F.; de Souza, A. M. T.; Craik, C. S.; Dias, L. R. S.; Castro, H. C.; Sathler, P. C. Eur. J. Med. Chem. 2017, 135, 213.
[18] Hoang, T. K. A.; Doan, T. N. L.; Cho, J. H.; Su, J. Y. J.; Lee, C.; Lu, C.; Chen, P. ChemSusChem 2017, 10, 3160.
[19] Wan, J. P.; Jing, Y. F.; Hu, C. F.; Sheng, S. R. J. Org. Chem. 2016, 81, 6826.
[20] Peloquin, D. M.; Schmedake, T. A. Coord. Chem. Rev. 2016, 323, 107.
[21] Devi, N.; Singh, D.; Rawal, R. K.; Bariwal, J.; Singh, V. Curr. Top. Med. Chem. 2016, 16, 2963.
[22] Goel, R.; Luxami, V.; Paul, K. Curr. Top. Med. Chem. 2016, 16, 3590.
[23] Hill, M. D. Synthesis 2016, 48, 2201.
[24] Benoit, R.; Dupas, G.; Bourguignon, J.; Queguiner, G. Synthesis 1987, 1124.
[25] Myers, J. T.; Hanna, J. M. Tetrahedron Lett. 2012, 53, 612.
[26] Komarova, E. S.; Makarov, V. A.; Granik, V. G.; Parkanyi, C. J. Heterocycl. Chem. 2012, 49, 969.
[27] Aggarwal, R.; Singh, G.; Kumar, S.; McCabe, T.; Rozas, I. ChemistrySelect 2016, 1, 5990.
[28] Hill, M. D.; Fang, H. Q.; Brown, J. M.; Molski, T.; Easton, A.; Han, X. J.; Miller, R.; Hill-Drzewi, M.; Gallagher, L.; Matchett, M.; Gulianello, M.; Balakrishnan, A.; Bertekap, R. L.; Santone, K. S.; Whiterock, V. J.; Zhuo, X. L.; Bronson, J. J.; Macor, J. E.; Degnan, A. P. ACS Med. Chem. Lett. 2016, 7, 1082.
[29] Smith, E. L.; Abbott, A. P.; Ryder, K. S. Chem. Rev. 2014, 114, 11060.
[30] Trivedi, T. J.; Lee, J. H.; Lee, H. J.; Jeong, Y. K.; Choi, J. W. Green Chem. 2016, 18, 2834.
[31] Liu, W.; Jiang, W.; Zhu, W. Q.; Zhu, W. S.; Li, H. P.; Guo, T.; Zhu, W. H.; Li, H. M. J. Mol. Catal. A:Chem. 2016, 424, 261.
[32] Pan, Y.; Alam, M. A.; Wang, Z. M.; Huang, D. L.; Hu, K. Q.; Chen, H. X.; Yuan, Z. H. Bioresour. Technol. 2017, 238, 157.
[33] del Monte, F.; Carriazo, D.; Serrano, M. C.; Gutierrez, M. C.; Ferrer, M. L. ChemSusChem 2014, 7, 999.
[34] Gonzalez-Martinez, D.; Gotor, V.; Gotor-Fernandez, V. Eur. J. Org. Chem. 2016, 1513.
[35] Wagle, D. V.; Zhao, H.; Baker, G. A. Acc. Chem. Res. 2014, 47, 2299.
[36] Li, X. X.; Row, K. H. J. Sep. Sci. 2016, 39, 3505.
[37] Liu, P.; Hao, J. W.; Mo, L. P.; Zhang, Z. H. RSC Adv. 2015, 5, 48675.
[38] Li, P. H.; Ma, F. P.; Wang, P.; Zhang, Z. H. Chin. J. Chem. 2013, 31, 757.
[39] Wang, P.; Ma, F. P.; Zhang, Z. H. J. Mol. Liq. 2014, 198, 259.
[40] Hu, H. C.; Liu, Y. H.; Li, B. L.; Cui, Z. S.; Zhang, Z. H. RSC Adv. 2015, 5, 7720.
[41] Zhang, M.; Liu, P.; Liu, Y. H.; Shang, Z. R.; Hu, H. C.; Zhang, Z. H. RSC Adv. 2016, 6, 106160.
[42] Liu, P.; Hao, J. W.; Zhang, Z. H. Chin. J. Chem. 2016, 34, 637.
[43] Zhang, M.; Liu, Y. H.; Shang, Z. R.; Hu, H. C.; Zhang, Z. H. Catal. Commun. 2017, 88, 39.
[44] Xiong, X. Q.; Han, Q.; Shi, L.; Xiao, S. Y.; Bi, C. Chin. J. Org. Chem. 2016, 36, 480(in Chinese). (熊兴泉, 韩骞, 石霖, 肖上运, 毕成, 有机化学, 2016, 36, 480.)
[45] Yan, N.; Xiong, Y. K.; Xia, J. H.; Rui, P. X.; Lei, Z. W.; Liao, W. L.; Xiong, B. Chin. J. Org. Chem. 2015, 35, 384(in Chinese). (严楠, 熊云奎, 夏剑辉, 芮培欣, 雷志伟, 廖维林, 熊斌, 有机化学, 2015, 35, 384.)
[46] Guo, R. Y.; Wang, P.; Wang, G. D.; Mo, L. P.; Zhang, Z. H. Tetrahedron 2013, 69, 2056.
[47] Li, B. L.; Zhang, M.; Hu, H. C.; Du, X.; Zhang, Z. H. New J. Chem. 2014, 38, 2435.
[48] Li, B. L.; Hu, H. C.; Mo, L. P.; Zhang, Z. H. RSC Adv. 2014, 4, 12929.
[49] Zhang, M.; Lu, J.; Zhang, J. N.; Zhang, Z. H. Catal. Commun. 2016, 78, 26.
[50] Zhang, H. Y.; Hao, X. P.; Mo, L. P.; Liu, S. S.; Zhang, W. B.; Zhang, Z. H. New J. Chem. 2017, 41, 7108.
[51] Zhang, M.; Fu, Q. Y.; Gao, G.; He, H. Y.; Zhang, Y.; Wu, Y. S.; Zhang, Z. H. ACS Sustainable Chem. Eng. 2017, 5, 6175.
[52] Zhang, M.; Han, Y.; Niu, J. L.; Zhang, Z. H. Adv. Synth. Catal. 2017, 359, 3618.
[53] Zhang, J. N.; Yang, X. H.; Guo, W. J.; Wang, B.; Zhang, Z. H. Synlett 2017, 28, 734.
[54] Gao, G.; Han, Y.; Zhang, Z. H. ChemistrySelect 2017, 2, 11561.
[55] Ma, C. T.; Liu, P.; Wu, W.; Zhang, Z. H. J. Mol. Liq. 2017, 242, 606.

低共熔溶剂催化一锅合成4,7-二氢-1H-吡唑并[3,4-b]吡啶-5-腈衍生物

Deep Eutectic Solvent Catalyzed One-Pot Synthesis of 4,7-Dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jing Huang, Yihua Yang, Zhanhui Zhang, Shouxin Liu. Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 409-420.
[2]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[3]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[4]	Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200) [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.
[5]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[6]	Baichuan Mo, Chunxia Chen, Jinsong Peng. Research Progress in Application of Lignin and Its Derivatives Supported Metal Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1215-1240.
[7]	Qiyang Li, Haiyan Zhang, Wenbo Liu. Research Progress in Transition-Metal-Free C—Si Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3470-3490.
[8]	Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang. Research Progress in Synthesis and Application of Thiosulfonates [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2322-2330.
[9]	Qingyun Gu, Zhenfeng Cheng, Xiaobao Zeng. Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1537-1544.
[10]	Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.
[11]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[12]	Yu Zheng, Shencheng Qian, Pengcheng Xu, Binnan Zheng, Shenlin Huang. Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4275-4281.
[13]	Anguo Ying, Linsheng Bai, Hailiang Hou, Songlin Xu, Xiaotong Lu, Limin Wang. Research on Thia-Michael Addition Tandem Reactions Catalyzed by AlCl₃@MNPs [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3843-3852.
[14]	Lulu Zheng, Yuqing Wang, Xiaogang Li, Wenbin Zhang. Deep Eutectic Solvent/Benzenesulfonic Acid: An Environmental Friendly Catalyst System towards the Synthesis of Dihydropyrimidinones via Biginelli Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3714-3720.
[15]	Hongxia Li, Peng Chen, Zhilin Wu, Yuhan Lu, Junmei Peng, Jingyang Chen, Weimin He. Electrochemical Oxidative Cross-Dehydrogenative Coupling of Five-Membered Aromatic Heterocycles with NH₄SCN [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3398-3404.